


The Initiation

by jocksplayhouse



Series: Elite Boy Band Initiates (E.B.B.I.) [1]
Category: One Direction (Band), PRETTYMUCH (Band), Real Person Fiction
Genre: Bottom Brandon Arreaga, M/M, Mentioned James Maslow, Mentioned Justin Timberlake, Mentioned Nick Carter, Mentioned Robbie Williams, Top Harry Styles
Language: English
Status: Completed
Published: 2020-10-23
Updated: 2020-10-23
Packaged: 2021-03-09 04:14:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,736
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27167755
Author URL: https://archiveofourown.org/users/jocksplayhouse/pseuds/jocksplayhouse
Summary: Brandon Arreaga had been hearing whispers about a secret club for boy band members and boy band alumni for months when he decided to get to the bottom of it. He asked his manager, Simon Cowell, to give him Harry Styles' phone number, another artist Simon previously managed.Brandon texted him, asking him if they could meet in person to talk, explaining that this was something better to discuss in person. Harry agreed in peak curiosity.
Relationships: Brandon Arreaga/Harry Styles
Series: Elite Boy Band Initiates (E.B.B.I.) [1]
Series URL: https://archiveofourown.org/series/1983067
Kudos: 2





	The Initiation

Brandon Arreaga had been hearing whispers about a secret club for boy band members and boy band alumni for months when he decided to get to the bottom of it. He asked his manager, Simon Cowell, to give him Harry Styles' phone number, another artist Simon previously managed.

Brandon texted him, asking him if they could meet in person to talk, explaining that this was something better to discuss in person. Harry agreed in peak curiosity. 

When, the two finally sat down together in Harry's New York apartment, Harry was quick to start the conversation. 

"So, what's this about, Brandon?"

The younger man shuffled in his seat awkwardly, not quite sure how to ask the question.

"Alright, so I don't know if this true or not, and you can laugh and shrug it off if not, but I just have to ask..." Brandon began.

Harry nodded. "Okay, go ahead."

"So...I heard there was this, like, secret club for boy band members and boy band alumni on the low...and I was just wondering if you know anything about or if it's real?" Brandon asked, treading on the topic lightly.

Harry grinned, chuckling slightly. Brandon just stared at him, awaiting his response. Harry finally opened his mouth.

"Yes."

Brandon raised an eyebrow. "Yes to what? Yes, you know about it? Or yes, it's real?"

"Both," said Harry.

Brandon ran his hand through his hair, his eyes widening. "I knew it!"

Harry smiled. Brandon leaned forward in his seat.

"Well, what do you know about it?"

Harry leaned forward to match Brandon's pose. 

"I'm in it." He confessed.

Brandon's jaw dropped in a shocked, but ecstatic, manner. "No way, you gotta get me in, please!"

Harry leaned back into the couch. "You can't just 'get in'. You have to be initiated in."

"Well, how do I do that?" The boy asked eagerly.

"How about we go to the lair and have it all explained there?" Harry suggested, raising an eyebrow, the corner of his lip curving upward.

"Fuck yeah!" Brandon replied giddily 

The trip was no easy feat. The pair had to board a private jet and fly from New York to a small island off the coast of California before they arrived at the remote "Elite Boy Band Initiates," also known as E.B.B.I. ( _e-bye_ ), resort.

Complete with a fence around the entire property and security guarding the premises, the building was swallowed by elusiveness, probably intended. From Brandon's first impression and perspective, it was a seclusive resort for the men to get away and retreat from the limelight and public eye for a while. He could see why so many alumni would want to partake in this club.

As they stepped inside the facility, they were welcomed by a reception type lobby. A man sat behind the front desk quickly noticed them and ushered the two over.

"Mr. Styles, welcome back."

Harry smiled. "Thank you, Alvin. May I see the key to basement floor?"

Alvin nodded and quickly grabbed a key from the drawer below him, handing it to Harry.  
Harry tipped his head and began walking towards the staircase, Brandon in tow.

"Basement floor?" Brandon inquired.

"Yes, basement floor. It's where all of the meetings and stuff go on. We have it reserved special for us," said Harry, winking at the confused boy behind him.

The duo now shuffled down the stairs, Harry stopping at the entrance to the basement. Brandon tripped into his back, not expecting him to stop before him.

"What?" Brandon asked confused.

Harry planted a hand on his shoulder. "This place is probably gonna surprise you and be a lot to take in. Just trust me?"

Brandon began to get nervous, but he nodded anyways. As Harry turned the key into the lock, he forcefully pushed the door open, exposing the hallway ahead. He smiled at Brandon and waved his hand, signaling him to enter first. Brandon began walking.

The hallway was dark. No overhead lights. Only lights hung alongside each picture frame lining the walls. It was then that Brandon began paying attention to the pictures hung in said frames. His eyes almost popped out of his head when he saw Justin Timberlake getting fucked in the picture before him.

"YO, WHAT THE FUCK?! Is that Justin Timberlake?!" He yelped, turning to see Harry's reaction.

Harry nodded. "Yeah, that was back in 2002 when he chose to get fucked by Robbie Williams so he could join this club and get out of his NSYNC contract."

Brandon's jaw dropped. " _Shit_. Whatever you gotta do to get where you wanna be in your career, I guess."

He shifted his head to the other side of the wall and saw James Maslow from Big Time Rush getting fucked.

"James Maslow?! Who's fucking him!? How the fuck did that happen?!" Brandon asked in utter shock.

Harry walked up beside the curious boy to look at the picture as well. "Nick Carter from the Backstreet Boys. It was in 2012. According to James, it was to assure he wouldn't fade into oblivion after Big Time Rush ended."

Brandon turned to him.

"I don't know how well it worked though." Harry laughed.

Brandon smiled. The next picture made him almost fall to the floor in surprise.

"HARRY, THAT'S YOU!!!"

Harry laughed as he looked at the picture of him getting pounded on the wall. "That's me."

Brandon placed his hands on each side of his face, trying to take it all in. "But why? When?"

"It was 2013. I'm actually the youngest member to be inducted. It was in January 2013, a few weeks before my 19th birthday. I don't know why. I guess I just kinda wanted a place to come chill when all the One Direction shit was getting annoying," said Harry chuckling.

Brandon elbowed Harry in the side, raising an eyebrow. "Who inducted you...?"

Brandon had noticed you couldn't see the faces of the tops in any of the hanging pictures and wondered if there was a reason for that.

"I'll tell you later, ONLY if you actually get inducted into the club." Harry responded ominously.   
Brandon suddenly remembered the reason he came.

To get inducted.

"Woah woah woah, wait, do I have to get fucked to join?"

Harry stopped and looked at him. "Well, yeah. That's how we all get initiated into the club. It's the rule."

Brandon sighed. " _Shit_...I didn't know that."

"You don't have to. It's up to you. You just won't be a member if you don't." Harry explained.

Brandon sighed even harder at that. He had never been fucked in the ass before. Hell, he'd never had sex with a man AT ALL before.

But he did really wanna join the club.

"Well, who would fuck me...?" Brandon questioned, debating.

"It could be me, if you want." Harry grinned, winking.

Brandon felt comfortable with Harry. He'd rather have Harry pounding him than some random boy band dude in his 40s.

"Fuck it, I'll do it!" Brandon finally agreed.

Harry pushed a curl out of the shorter boy's face. "You sure?  
"  
Brandon grinned. "Fuck yeah. Initiate me."

Harry smiled and guided him into a bedroom around the corner. The room was dimly light, saturated in sexual decoration, from the satin sheets to the lube and condoms sitting on the nightstand beside the bed.

"Now before we do this, I gotta tell you the rules and everything you need to know." Harry said, catching Brandon off guard.

"Okay. What are they?"

Harry sat on the edge of the bed, patting the empty space beside him. Brandon sat down next to him.

"First off, you decide how sensual you want it to be. We can make out and shit or I can just plow you with no romantic actions involved."

Brandon nodded. "Okay."

"Secondly, there's a camera on the wall over there. You're gonna look at it when I'm fucking you and a red dot will blink three times to signal a picture is being taken. I'm gonna have my head behind your back because tops are never in the picture."

"I noticed that in the pictures in the hallway. Why is that?" Brandon asked  
.  
"Well, the pictures are taken so you won't speak to the public about the club. The club is a secret. So if you speak out about it, not only do you get kicked out, but the picture of you getting fucked is leaked too. It's incentive." Harry explained.

Brandon scratched his eyebrow. "Well, fuck. Won't do that then."

Harry chuckled.

Harry began undressing and Brandon followed nervously. When the two were in nothing but their underwear, Brandon looked up at Harry as he towered over him. His eyes traveled over his ripped body and many tattoos. He was ready to see his cock, just to see how big the appendage going inside of him would be.

Harry must have been able to tell what Brandon was thinking because he slid the black boxer briefs to his knees, his large 9 inch cock flopping out with a pop.

Brandon's eyes were as big as saucers now. " _Shit!_ I gotta take that up the ass?!"

Harry laughed. "I'll start slow, work your hole over with my fingers if you want."

"Please." He replied.

Harry chuckled. Suddenly, his fingertips were wrapped around each of Brandon's thighs as he pushed him backwards onto the bed, pushing him up to the pillows.

Brandon gasped in surprise. Harry tugged on the waistband of Brandon's red boxer briefs.

"Can I take these off now?"

Brandon nodded, lifting his waist into the air so Harry could slide them off. Harry quickly pulled the underwear off of the boy below him and tossed them onto the carpet.

"Spread." He commanded.

"What?" Brandon said unsure.

"Your legs. Spread your legs." Harry clarified. 

"Oh," said Brandon, as he slowly separated his legs.

Harry leaned over, grabbing the lube off the nightstand. Opening the top, he squired a glob onto his fingers and began rubbing a circle around Brandon's hole.

Brandon gasped. " _Woah!_ It's cold."

Harry chuckled. "Sorry."

Brandon grinned. "All good."

It was then that Harry pushed a finger inside. 

" _SHIT!_ " Brandon yelped.

Harry didn't apologize this time. Instead, he just grinned at the boy squirming on the bed at his hand.  
As Harry worked his hole over for a few minutes, he added a finger. And then another. And suddenly, there were three fingers going in and out of Brandon's boypussy.

And although Brandon claimed to be straight many times, even once or twice as he laid on this hotel bed, he began taking control of the fuck, sliding himself down on Harry's fingers. Perhaps he wasn't as straight as he'd been aiming for everyone to believe...

Harry suddenly slipped his wet fingers out with a _pop!_ sound.

"Ready for my cock, Arreaga?" He asked seductively. 

Brandon nervously gulped, looking down at the 9 inch dick eyeing him. "Y-yeah."

Harry shot him a smirk as he started climbing onto the bed, his body hovering over the boy below him. With one hand on the bedpost for support, he began aligning his member with Brandon's lubed up hole.

Leaning down to Brandon's face, Harry said, "You can dig your fingers into my back if you want. It'll help with the pressure."

Brandon nodded nervously. 

With no warning, Harry rammed his member inside of Brandon, slamming his prostate hard.  
" _AHHHH, FUCK!_ " Brandon moaned loudly, his yelp reverberating off the walls. His nails dug into Harry's back instantly.

"Sorry, bro. Figured I'd just shove it in like ripping off a band aid." Harry apologized.

Brandon's breathing slowed as he placed a hand on his head, flexing. "It's fine, just give me some warning next pound, dude."

Harry grinned. "Got it."

As he looked up at Harry's glistening face and body, his brown hair falling in his face, Brandon couldn't help but give into his temptation.

"W...Would you kiss me...? I just figure if I'm doing this, go all in, right?" He asked timidly. 

Harry bit his lip, smiling. "Hell yeah, mate."

Leaning in, Harry began kissing his first time bottom, tongue and all. Brandon would never admit it, but he fucking loved this kiss. Harry's lips were different than any woman's he'd tasted. Harry's were more forceful and seductive. They tasted amazing. Brandon almost wondered if he'd get high off those lips cause it felt like ecstasy running through his body.

Harry slowly began pushing in and out of Brandon, Brandon wincing and moaning with each thrust.  
Suddenly, Harry pulled out to Brandon's confusion.

"Get on your stomach." He commanded.

"Why?" Brandon asked confused.

"I'm gonna show you the art of doggystyle. Get on your stomach, Arreaga."

Both Brandon's hole and cock quivered at Harry's commanding tone. 

Oddly, he liked being told what to do...

"Okay." He said, flipping onto his stomach.

Harry pulled his ass into the air. Brandon gasped at the forceful tug. He was being manhandled by Harry Styles of all people and he couldn't help but enjoy all of it.

What the fuck was going on with his body? He's straight...

But as Harry began pounding his hole doggystyle, his high pitched moans of pleasure might beg to differ...

" _Fuck! Shit! Fuck! Mmm, Harry! UGH!_ " He yelped out with each slam to his prostate.

Harry smirked knowing he was stretching out the "straight" boy and he was loving every minute of it.  
As Brandon took all 9 inches of Harry's cock, base to tip, he realized this was the best fuck of his life  
.  
But he's straight, and this is a dude. A dude fucking HIS ass. 

He didn't have time to dwell in that though cause now Harry was thrusting Brandon on top of him now, so that he was in a riding position, bouncing up and down on Harry's cock.

" _Fuuuuuuck_ , bro." He moaned, his voice cracking.

His cheeks turned red at the embarrassing squeak. 

Harry chucked silently. _Not so manly now, huh?_ He thought.

"Smile for the camera, bitch," says Harry out of the blue.

It's now that Brandon realizes the most emasculating moment of his life, him taking 9 inches of cock up ass, is now being photographically documented forever.

Even worse, as he looks down, he notices that his cock is hard and leaking. He promised himself he wouldn't get hard. He was straight. So he didn't touch himself, he didn't jerk off at all during this fuck, and somehow he STILL got hard.

As Harry wrapped his strong arm around Brandon's chest, grabbing his pec, he slammed into Brandon as hard as he could. 

And with that slam, Brandon busted, coming all over himself, Harry, the bed, and even a little onto the floor beside their clothes, just as the camera took the picture, catching Brandon's biggest (and best) orgasm.

Brandon's cheeks were bright red with embarrassment now. He couldn't say anything. So he didn't.

Until Harry did, right after he shot his load into the condom, Brandon getting goosebumps at the warm sensation inside him, for the first time ever, that he kinda liked...

"You came first," He laughed. "Must have enjoyed it more than you expected."

"Shut up!" Brandon yelled in humiliation.

"Would you feel better if I told you who I bottomed for to get into the club...?" Harry asked, winking, trying to make the boy feel better.

Brandon perked up at the question. "Yeah."

"Justin Timberlake." Harry finally confessed.

Brandon's eyes raised and a smile formed on his face. "I knew it!!"

Harry rolled his eyes playfully. "Did not."

"Did too." Brandon argued.

"Whatever," said Harry. "You know what he told me though?"

"What?" Brandon questioned in interest.

"He told me that if you're still currently in a boy band when you get initiated, you have to get fucked twice..."

And then Harry wrapped a hand around Brandon's cock, the first time Brandon had had a man's hand around his dick ever.

He looked down at Harry's hand on his cock and then thought about the orgasm he just had. Maybe he wasn't _completely_ straight...

"Fuck it," he said grinning, lifting his legs in the air for Harry to grab and pound him once more.

And two times became three. And three turned into four. And before he knew it, Brandon was getting fucked by Harry at least once a month here in this very bedroom.

A true resort regular...


End file.
